It’s Your First Time Together: Here’s 5 Things He’s Thinking

A couple weeks ago, I was having a beer (fine, it was an earl grey martini) with my friend Natalie who a few months ago, broke things off with her fiance. Natalie was excited because after the requisite months of mourning, crying, etc., she had started dating again, had kissed a few boys and was getting ready for the main event—for the first time in years, she was going to sleep with a guy who wasn’t her ex. She was all giggles and jokes, but also quite nervous. I understood, as much fun as it is to learn a new body, hear all new sounds, and create some new harmonies, it’s a little terrifying for guys as well. Here are five things running through our minds before the big launch (this would be the night of, when things are getting going):

1. Can she see my boner? Both literally and figuratively, this is a worry. Sex is never a sure thing, and we’re constantly fretting that our aggressiveness or eagerness will be a turn-off. I’m not for playing games, but there’s a part of me that wants her to think I’m only so into it until game time. I want her thinking “Is he going to kiss me?”

2. Do I want to sleep over? / Do I want her to sleep over? There’s a bigger question here: Do I really like her? Sleepovers can be complicated. They tend to mean more than sex, because there is the next morning to contend with. But the night before, she’s back at my place, we’re having cocktails, there’s touching; seems hardly the right for a “where do we stand,” chat. Then again, when is?

3. I hope I don’t embarrass myself taking off her bra. I swear I’ve done this before ..oy. Even when she laughs and snaps it off with the flick of a thumb and forefinger, for the few seconds before, we feel like total losers. It’s a vibe killer when we fail at the bra clasp. A mild one. But a vibe killer nonetheless. And we know it.

4. Can she see my boner? (part 2) This is a size issue. Am I so small that she can’t even see it? Am I so big that it’s all she can see and it is scaring her? In all honesty, I’ve been on both sides of this Goldilocks equation (though not to either extreme) but not often. It’s all relative, and only matters so much. Ultimately, this question doesn’t really bother me, for the following reason: I figure she wants to be with the guy who moves and acts like that kind of thing has never occurred to him. 5. Oh My God. I Get To See Her Naked. All those things that you’re worrying about are wasted thoughts. We’re excited. Trust me.

So now you have some insight into what's going on in our testosterone-filled brains when we're working towards the main event. After the bell has rung, there's a whole other set of thoughts.